Spiro[1,3-dioxolane-2,8′(5’H)-[2H-2,4a]methanonaphthalene],hexahydro-1′,1′,5′,5′-tetramethyl-, [2’S-(2′.alpha.,4’a.alpha.,8’a.alpha.)]- (CAS 154171-77-4) — Woody Base Note Fragrance Ingredient
Spiro[1,3-dioxolane-2,8'(5'H)-[2H-2,4a]methanonaphthalene],hexahydro-1',1',5',5'-tetramethyl-, [2'S-(2'.alpha.,4'a.alpha.,8'a.alpha.)]-
CAS 154171-77-4
What Is Spiro[1,3-dioxolane-2,8'(5'H)-[2H-2,4a]methanonaphthalene],hexahydro-1',1',5',5'-tetramethyl-, [2'S-(2'.alpha.,4'a.alpha.,8'a.alpha.)]-?
This synthetic compound is a specialized fragrance ingredient used in modern perfumery. It’s found in niche and designer fragrances seeking unique woody-ambery effects. As a synthetic molecule, it offers perfumers precise control over scent profiles and stability in formulations.
Safety Profile
USE WITH AWARENESSWhat Does Spiro[1,3-dioxolane-2,8'(5'H)-[2H-2,4a]methanonaphthalene],hexahydro-1',1',5',5'-tetramethyl-, [2'S-(2'.alpha.,4'a.alpha.,8'a.alpha.)]- Smell Like?
This molecule delivers a complex woody-ambergris character with subtle marine undertones. Initially presenting a crisp, almost ozonic top note, it evolves into a warm, musky heart reminiscent of sun-bleached driftwood. The dry-down reveals a sophisticated ambery base with lingering hints of dry tobacco leaves and a whisper of salty sea air.
2D Molecular Structure
SMILES: [H][C@]12C(C)(C)[C@H]3CC[C@@]1(C3)C(C)(C)CCC21OCCO1
Chemistry, Properties & Perfumer Guide
The Chemistry
This spirocyclic compound belongs to the family of synthetic amber molecules designed to mimic natural ambergris characteristics. The complex bicyclic structure provides excellent stability and longevity in fragrance applications. Synthesis typically involves multi-step cyclization reactions starting from terpene precursors, with careful control of stereochemistry to achieve the desired olfactory profile.
Physical & Chemical Properties
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Fine Fragrance | 0.5-2% | Up to 5% | Amber base note enhancer |
| Functional Fragrance | 0.1-0.5% | Up to 1% | Stability concerns at higher levels |
Classic Accords
Tip: Use with ionones to soften the woody character and enhance diffusion.
Alternatives & Comparisons
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
No specific IFRA restrictions currently apply to this material.
RIFM Assessment
Full safety assessment pending through RIFM.
Sustainability
As a synthetic material, this compound avoids harvesting pressures on natural resources. Production requires careful solvent management and energy inputs typical for complex organic synthesis. Future green chemistry approaches may improve its environmental profile.
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Ingredient Data Sheet
CAS 154171-77-4Physical Properties
| Molecular Weight | 264.4 g/mol🔬 PubChem |
| LogP (Octanol-Water) | 4.4🔬 PubChem |
| Boiling Point | 280 °C🔬 EPA CompTox |
| Vapor Pressure | 0.0044 mmHg @ 25°C📊 OPERA |
| Flash Point | 105.1 °C🔬 EPA CompTox |
| Involatility Index | 0.0003💻 Calculated |
| log Kp (skin permeability) | -1.189💻 Calculated |
| SMILES | CC1(CCC2(C3C14CCC(C4)C3(C)C)OCCO2)C🔬 PubChem |
Volatility & Performance
| Fragrance Note | Base💻 Calculated |
| Volatility Class | Very slow💻 Calculated |
| Persistence Score | 5.7 / 5💻 Calculated |
Odor & Flavor
| Functional Groups | ether💻 RDKit |
Physical data: PubChem (NIH/NLM), U.S. EPA CompTox Dashboard, EPA OPERA models, RDKit. Odor & flavor: Arctander (Perfume & Flavor Chemicals), Fenaroli's Handbook of Flavor Ingredients, Leffingwell. Thresholds: van Gemert (Compilations of Odour Threshold Values). Regulatory: IFRA Standards 51st, FEMA GRAS. Trade names: Surburg (Common Fragrance & Flavor Materials). All data compiled and cross-referenced for perfumertools.com.
Physicochemical Properties
DTXSID: DTXSID6051350
Physical Properties
| Molecular Weight | 264.409 g/mol🔬 EPA CompTox |
| Density | 1.022 g/cm^3📊 OPERA |
| Boiling Point | 280 °C🔬 EPA CTX |
| Melting Point | 58.805 °C📊 OPERA |
| Flash Point | 114.697 °C📊 OPERA |
| Refractive Index | 1.524 Dimensionless📊 OPERA |
| Molar Volume | 248.773 cm^3/mol📊 OPERA |
Partition & Solubility
| LogP (Octanol-Water) | 5.69 Log10 unitless🔬 EPA CTX |
| LogD (pH 5.5) | 5.084 Log10 unitless📊 OPERA |
| LogD (pH 7.4) | 5.084 Log10 unitless📊 OPERA |
| LogKoa (Octanol-Air) | 8.41 Log10 unitless📊 OPERA |
| Water Solubility | 0 mol/L🔬 EPA CTX |
| Henry's Law Constant | 0 atm-m3/mole📊 OPERA |
Transport Properties
| Vapor Pressure | 0.004 mmHg🔬 EPA CTX |
| Surface Tension | 36.164 dyn/cm📊 OPERA |
Molecular Descriptors
| Topological Polar Surface Area | 18.46 Ų💻 Computed |
| H-Bond Donors | 0 count💻 Computed |
| H-Bond Acceptors | 2 count💻 Computed |
| Rotatable Bonds | 0 count💻 Computed |
| Aromatic Rings | 0 count💻 Computed |
| Molar Refractivity | 76.06 cm^3/mol📊 OPERA |
| Polarizability | 30.153 Å^3📊 OPERA |
Data Sources:
🔬 EPA Experimental data from U.S. EPA CompTox Chemicals Dashboard & CTX APIs. 📊 OPERA Predicted using EPA's OPERA QSAR models. 💻 Computed Calculated from SMILES using RDKit.
